2-Pyridinemethanamine → (R)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-2-ylmethyl)thiazole-5-carboxamide

HRID 554955

反応式

HRID 554955 の反応式
N1C=CC=C(CN)C=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][NH2:16].[F:17][C:18]1[CH:40]=[CH:39][C:21]([CH2:22][N:23]2[C@@H:27]([CH3:28])[CH2:26][N:25]([C:29]3[S:30][C:31]([C:35](O)=[O:36])=[C:32]([CH3:34])[N:33]=3)[C:24]2=[O:38])=[CH:20][CH:19]=1.FC1C=CC(CN2[C@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1>>[F:17][C:18]1[CH:40]=[CH:39][C:21]([CH2:22][N:23]2[C@H:27]([CH3:28])[CH2:26][N:25]([C:29]3[S:30][C:31]([C:35]([NH:16][CH2:15][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=4)=[O:36])=[C:32]([CH3:34])[N:33]=3)[C:24]2=[O:38])=[CH:20][CH:19]=1

参加物

5

反応物 4

HCID 195092-PyridinemethanamineHCID 310183-PyridinemethanamineHCID 57919880HCID 57919880、化合物HCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

生成物 1

HCID 57919929(R)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-2-ylmethyl)thiazole-5-carboxamide

実験手順

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with pyridin-2-ylmethanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (R)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid (48%): mp 118-119° C. (ethanol/water); 1H NMR (300 MHz, DMSO-d6) δ 8.54-8.50 (m, 2H), 7.79-7.75 (m, 1H), 7.40-7.16 (m, 6H), 4.60 (d, J=15.6 Hz, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.31 (d, J=15.6 Hz, 1H), 4.20 (dd, J=10.0, 9.2 Hz, 1H), 3.79-3.72 (m, 1H), 3.56 (dd, J=10.0, 6.8 Hz, 1H), 2.49 (s, 3H), 1.23 (d, J=6.1 Hz, 3H); MS (ES+) m/z 439.9 (M+1).

出典と根拠

ORDレコード
ord-a59c14be0b8d4802b9107803845af494
出典データセット
uspto-grants-2011_11
特許番号
US08049016B2

関連ノート

読み込み中…